Triclabendazole

Chemical compound

  • US DailyMed: Triclabendazole
Routes of
administrationBy mouthATC code
  • P02BX04 (WHO) QP52AC01 (WHO)
Legal statusLegal status
  • US: ℞-only
Pharmacokinetic dataMetabolismOxidation to sulfone and sulfoxide metabolitesElimination half-life22–24 hoursExcretionFeces (>95%), urine (2%), milk (<1%)Identifiers
  • 5-Chloro-6-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole
CAS Number
  • 68786-66-3 ☒N
PubChem CID
  • 50248
ChemSpider
  • 45565 checkY
UNII
  • 4784C8E03O
KEGG
  • D07364 ☒N
ChEMBL
  • ChEMBL1086440 checkY
CompTox Dashboard (EPA)
  • DTXSID7043952 Edit this at Wikidata
ECHA InfoCard100.127.414 Edit this at WikidataChemical and physical dataFormulaC14H9Cl3N2OSMolar mass359.65 g·mol−13D model (JSmol)
  • Interactive image
Melting point175 to 176 °C (347 to 349 °F)
  • CSc3nc2cc(Cl)c(Oc1cccc(Cl)c1Cl)cc2[nH]3
  • InChI=1S/C14H9Cl3N2OS/c1-21-14-18-9-5-8(16)12(6-10(9)19-14)20-11-4-2-3-7(15)13(11)17/h2-6H,1H3,(H,18,19) checkY
  • Key:NQPDXQQQCQDHHW-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Triclabendazole, sold under the brand name Egaten among others, is a medication used to treat fascioliasis and paragonimiasis.[1] It is very effective for both conditions.[1] Treatment in hospital may be required.[1] It is taken by mouth with typically one or two doses being required.[1]

Side effects are generally few, but can include abdominal pain and headaches.[1] Biliary colic may occur due to dying worms.[2] While no harm has been found with use during pregnancy, triclabendazole has not been studied well in this population.[2] It is a member of the benzimidazole family of medications for worms.[1]

Triclabendazole was approved for medical use in the United States in 2019.[3][4] It is on the World Health Organization's List of Essential Medicines.[5] For human use, it can be obtained from the World Health Organization.[2] It is also used in animals.[6]

Chemistry

It is a member of the benzimidazole family of anthelmintics. The benzimidazole drugs share a common molecular structure, triclabendazole being the exception in having a chlorinated benzene ring but no carbamate group. Benzimidazoles such as triclabendazole are generally accepted to bind to beta-tubulin therefore preventing the polymerization of microtubules.[citation needed]

History

Since late 1990s, triclabendazole became available as a generic drug, as patents expired in many countries. Many products were developed then. Among them, Trivantel 15, a 15% triclabendazole suspension, was launched by Agrovet Market Animal Health in the early 2000s. In 2009, the first triclabendazole injectable solution (combined with ivermectin) was developed and launched, also by Agrovet Market Animal Health. The product, Fasiject Plus, a triclabendazole 36% and ivermectin 0.6% solution, is designed to treat infections by Fasciola hepatica (both immature and adult liver flukes), roundworms and ectoparasites, as well.[citation needed]

Fasinex is a brand name for veterinary use while Egaten is a brand name for human use.[citation needed]

References

  1. ^ a b c d e f World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. pp. 94, 96. hdl:10665/44053. ISBN 9789241547659.
  2. ^ a b c Wolfe MM, Lowe RC (2014). "Benzimidazoles". Pocket Guide to GastrointestinaI Drugs. John Wiley & Sons. p. PT173. ISBN 9781118481554. Archived from the original on 20 December 2016.
  3. ^ "Drug Trials Snapshots: Egaten". U.S. Food and Drug Administration (FDA). 13 February 2019.
  4. ^ "Egaten (triclabendazole)" (PDF). FDA. Retrieved 18 February 2019.
  5. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  6. ^ "Triclabendazole". Drugs.com. Archived from the original on 20 December 2016. Retrieved 10 December 2016.

Further reading

  • "Report of the WHO Informal Meeting on use of triclabendazole in fascioliasis control" (PDF). World Health Organization (WHO). 2006.
  • v
  • t
  • e
Antiplatyhelmintic agents
Antitrematodals
(schistosomicides)
Binds tubulin
AChE inhibitor
Other/unknown
Anticestodals
(taeniacides)
Binds tubulin
Other/unknown
Antinematodal agents
(including
macrofilaricides)
Binds tubulin
Glutamate-gated chloride channel, GABA receptor
NMDA
Other/unknown
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